Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole
Schmidt A, Habeck T, Snovydovych B, Eisfeld W (2007)
ORGANIC LETTERS 9(18): 3515-3518.
Zeitschriftenaufsatz
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Autor*in
Schmidt, Andreas;
Habeck, Tobias;
Snovydovych, Bohdan;
Eisfeld, WolfgangUniBi 
Einrichtung
Abstract / Bemerkung
Thermal decarboxylation converts 1,2-dimethylindazolium-3-carboxylate into indazol-3-ylidene, which reacts in situ with ketones to form stable 1:1 adducts. When the reaction is conducted with aromatic aldehydes in alcohols, redox esterifications to benzoates are observed. Model reactions such as redox esterifications of aromatic aldehydes with sodium alcoholates in the presence of 1,2-dimethylindazolium salt and oxidations of sodium benzylates by 1,2-dimethylindazolium salt to aldehydes lend support to a Cannizzaro-type mechanism of this reaction.
Erscheinungsjahr
2007
Zeitschriftentitel
ORGANIC LETTERS
Band
9
Ausgabe
18
Seite(n)
3515-3518
ISSN
1523-7060
eISSN
1523-7052
Page URI
https://pub.uni-bielefeld.de/record/1632757
Zitieren
Schmidt A, Habeck T, Snovydovych B, Eisfeld W. Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS. 2007;9(18):3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., & Eisfeld, W. (2007). Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS, 9(18), 3515-3518. https://doi.org/10.1021/ol0713739
Schmidt, Andreas, Habeck, Tobias, Snovydovych, Bohdan, and Eisfeld, Wolfgang. 2007. “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”. ORGANIC LETTERS 9 (18): 3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., and Eisfeld, W. (2007). Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS 9, 3515-3518.
Schmidt, A., et al., 2007. Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS, 9(18), p 3515-3518.
A. Schmidt, et al., “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”, ORGANIC LETTERS, vol. 9, 2007, pp. 3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., Eisfeld, W.: Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS. 9, 3515-3518 (2007).
Schmidt, Andreas, Habeck, Tobias, Snovydovych, Bohdan, and Eisfeld, Wolfgang. “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”. ORGANIC LETTERS 9.18 (2007): 3515-3518.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
11 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
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Ning Y, Kawahata M, Yamaguchi K, Otani Y, Ohwada T., Chem Commun (Camb) 54(15), 2018
PMID: 29392251
Ning Y, Kawahata M, Yamaguchi K, Otani Y, Ohwada T., Chem Commun (Camb) 54(15), 2018
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Cross-dehydrogenative coupling for the intermolecular C-O bond formation.
Krylov IB, Vil' VA, Terent'ev AO., Beilstein J Org Chem 11(), 2015
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Krylov IB, Vil' VA, Terent'ev AO., Beilstein J Org Chem 11(), 2015
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Elemental step thermodynamics of various analogues of indazolium alkaloids to obtaining hydride in acetonitrile.
Lei NP, Fu YH, Zhu XQ., Org Biomol Chem 13(47), 2015
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Lei NP, Fu YH, Zhu XQ., Org Biomol Chem 13(47), 2015
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Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles.
Guan Z, Namyslo JC, Drafz MH, Nieger M, Schmidt A., Beilstein J Org Chem 10(), 2014
PMID: 24778738
Guan Z, Namyslo JC, Drafz MH, Nieger M, Schmidt A., Beilstein J Org Chem 10(), 2014
PMID: 24778738
Pericyclic rearrangements of N-heterocyclic carbenes of indazole to substituted 9-aminoacridines.
Guan Z, Wiechmann S, Drafz M, Hübner E, Schmidt A., Org Biomol Chem 11(21), 2013
PMID: 23613125
Guan Z, Wiechmann S, Drafz M, Hübner E, Schmidt A., Org Biomol Chem 11(21), 2013
PMID: 23613125
N-heterocyclic carbene-catalyzed aerobic oxidative direct esterification of aldehydes with organoboronic acids.
Meng JJ, Gao M, Wei YP, Zhang WQ., Chem Asian J 7(5), 2012
PMID: 22454334
Meng JJ, Gao M, Wei YP, Zhang WQ., Chem Asian J 7(5), 2012
PMID: 22454334
One-pot synthesis of novel 2,3-dihydro-1H-indazoles.
Breton GW, Lepore AJ., Molecules 16(11), 2011
PMID: 22089862
Breton GW, Lepore AJ., Molecules 16(11), 2011
PMID: 22089862
A versatile catalyst system for Suzuki-Miyaura syntheses of sterically hindered biaryls employing a cyclobutene-1,2-bis(imidazolium) salt.
Schmidt A, Rahimi A., Chem Commun (Camb) 46(17), 2010
PMID: 20386846
Schmidt A, Rahimi A., Chem Commun (Camb) 46(17), 2010
PMID: 20386846
Functionalized 4-aminoquinolines by rearrangement of pyrazole N-heterocyclic carbenes.
Schmidt A, Münster N, Dreger A., Angew Chem Int Ed Engl 49(15), 2010
PMID: 20229542
Schmidt A, Münster N, Dreger A., Angew Chem Int Ed Engl 49(15), 2010
PMID: 20229542
Imidazol-2-and-4-ylidene by decarboxylation. Studies on the cross-conjugated mesomeric betaine-alkaloid norzooanemonine and its pseudo-cross-conjugated isomer.
Schmidt A, Beutler A, Albrecht M, Snovydovych B, Ramírez FJ., Org Biomol Chem 6(2), 2008
PMID: 18174998
Schmidt A, Beutler A, Albrecht M, Snovydovych B, Ramírez FJ., Org Biomol Chem 6(2), 2008
PMID: 18174998
One-pot oxidative esterification and amidation of aldehydes.
Ekoue-Kovi K, Wolf C., Chemistry 14(21), 2008
PMID: 18523938
Ekoue-Kovi K, Wolf C., Chemistry 14(21), 2008
PMID: 18523938
References
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